1. Technical Field
The present invention relates to a new bis-(hydroxybenzaldehyde) compound and a new polynuclear polyphenol compound derived therefrom, and specifically to a bis-(hydroxybenzaldehyde) compound (also referred to as bis-(formyl phenol) compound) having a formyl hydroxyphenyl group, via a methylene group, in the ortho position with respect to the hydroxyl group in the hydroxyphenyl nucleus at the center of the molecule, as well as a polynuclear polyphenol compound comprising the aforementioned compound with a phenol further bonded to the formyl groups at both ends.
More specifically, the present invention relates to a 2,6-bis-[(formyl hydroxyphenyl)methyl]-4-alkyl phenol compound having two formyl hydroxyphenyl groups mutually bonded, via a methylene group, to a p-alkyl substituted phenol; or a bis-(hydroxybenzaldehyde) compound having two hydroxybenzaldehyde groups mutually bonded, via a methylene group, to a polyphenol skeleton, where a cyclohexyl substituted group with excellent lipophilic property is included in the two phenol nucleuses of cyclohexyl bis-phenol; as well as a hydroxybenzil substituted polynuclear polyphenol compound derived therefrom.
These compounds are useful as component materials for photosensitive resist compositions, component materials and hardeners for epoxy resins, developers and anti-fading agents used in thermosensitive recording materials, bactericides, fungicides, antioxidants and other functional chemical products or component materials thereof.
2. Prior Art
Traditionally, bis-phenol compounds have been used widely as component materials for photosensitive resists, component materials and hardeners for epoxy resins, component materials for phenol resins, developers and anti-fading agents used in thermosensitive recording materials, bactericides, fungicides, and antioxidants, among others, as well as component materials thereof.
In recent years, demand for finer processing is requiring improvements in various performance properties such as higher sensitivity, higher resolution and greater development property for photosensitive resin materials, among others, in certain fields such as electronic components. In these fields, a number of new bis-phenol compounds have been proposed to address the demand for resist resins offering higher performance and function. For example, derivatives having a polynuclear aromatic compound as their skeleton are drawing the attention in the area of electron beam lithography, etc.
Among these bis-phenol compounds, of particular interest are bis-(hydroxybenzaldehyde) compounds obtained by using, as one component material, a 2,6-dimethylol-4-alkyl phenol obtained by reacting a p-alkyl phenol with a formaldehyde, and then reacting the material with various formyl substituted phenol compounds, because such bis-(hydroxybenzaldehyde) compounds have three aromatic nucleuses, possess a symmetrical molecular structure around the p-alkyl phenol nucleus at the center of the molecule, and also have functional groups including one hydroxyl group in the p-alkyl phenol nucleus at the center of the molecule and two phenolic hydroxyl groups and formyl groups at the ends of the molecule. These bis-phenol compounds are expected to offer improved levels of various reactivities and solubility in organic solvents, and therefore using them as component materials will likely create materials exhibiting improved heat resistance, water resistance, moisture absorption resistance and lower dielectric constant, among others.
Several bis-(formylphenol) compounds having such symmetrical structure are already known.
For example, Helvetica Chimica Acta (2003), 86 (7), 2396-2403 discloses 2,6-di(5-formyl-2-hydroxyphenyl)methyl-4-chlorophenol synthesized from a substituted phenol and 2,6-dihydroxy methyl-4-chlorophenol under irradiation of electron beam using zinc chloride as a catalyst or in a methanol solvent using hydrochloric acid as a catalyst. Another example is Japanese Patent Laid-open No. 2000-1448 that describes hydroxymethyl substituted 1,1-bis-cyclohexane, which is used as a component material for the bis-(hydroxybenzaldehyde) compound proposed by the present invention.
Also, Japanese Patent Laid-open No. Hei 11-199533 describes polynuclear polyphenol compound constituted by trisphenol skeletons of trisphenol methane type mutually bonded via a methylene group.
Patent Literature 1: Japanese Patent Laid-open No. 2000-1448
Patent Literature 2: Japanese Patent Laid-open No. Hei 11-199533
Non-patent Literature 1: Helvetica Chimica Acta (2003), 86 (7), 2396-2403